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Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions
Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in D...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055228/ https://www.ncbi.nlm.nih.gov/pubmed/35517475 http://dx.doi.org/10.1039/d0ra04592f |
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author | Chen, Xin Bian, Yunyun Mo, Baichuan Sun, Peng Chen, Chunxia Peng, Jinsong |
author_facet | Chen, Xin Bian, Yunyun Mo, Baichuan Sun, Peng Chen, Chunxia Peng, Jinsong |
author_sort | Chen, Xin |
collection | PubMed |
description | Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)(2)/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO(4) and KHCO(3). Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. |
format | Online Article Text |
id | pubmed-9055228 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90552282022-05-04 Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions Chen, Xin Bian, Yunyun Mo, Baichuan Sun, Peng Chen, Chunxia Peng, Jinsong RSC Adv Chemistry Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)(2)/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO(4) and KHCO(3). Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. The Royal Society of Chemistry 2020-06-30 /pmc/articles/PMC9055228/ /pubmed/35517475 http://dx.doi.org/10.1039/d0ra04592f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Chen, Xin Bian, Yunyun Mo, Baichuan Sun, Peng Chen, Chunxia Peng, Jinsong Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title | Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title_full | Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title_fullStr | Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title_full_unstemmed | Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title_short | Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions |
title_sort | copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential chan–lam and cross-dehydrogenative coupling reactions |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055228/ https://www.ncbi.nlm.nih.gov/pubmed/35517475 http://dx.doi.org/10.1039/d0ra04592f |
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